Sales Coaching Software Evaluation Guide

We’ve seen the good, the bad and the ugly. Here are the most important features that you should be looking for in your sales coaching software solution to support your field sales team.


5 Must-Have Features to Support Your Field Sales Team

Most sales leaders and sales enablement executives recognize how important front-line sales manager coaching is to reducing onboarding time for new reps, increasing sales rep productivity and reducing churn.

Life has gotten easier in the last few years for sales leaders running inside/remote sales teams with the recent proliferation of conversational intelligence platforms like gong.io, MindTickle and Chorus.ai allowing call recording.

But if you’re running a field sales team (more typical for complex B2B sales), where critical meetings generally happen in person and call recording in front of the customer isn’t generally possible, you’re still relying on your front-line managers to build the capabilities of your field sales team. And in our experience, front-line sales managers’ coaching skills are often the weakest link.

In this article, we’ll start with the challenges that front-line field sales managers face in this role, and then look at what we believe are the most critical features and capabilities of sales coaching software to help address these challenges, then consider key considerations for successful deployment to your field sales team.

The Front-Line Manager Coaching Dilemma

The promotion from an individual contributor to a sales manager is the hardest step-up in a sales career. Almost every sales manager is promoted into that role because they were a great salesperson.

But effective sales coaching is a very different skill to selling; unfortunately, most front-line managers remain great sales people but never develop strong coaching skills.

Most sales managers behave more like “Super-Reps” than coaches. Bridging this gap that presents the biggest benefit from deploying sales coaching software.

The main coaching gaps that we see, (and the areas that a great sales coaching platform can really add value) are:


  • Manager mindset – the single biggest gap – a lack of true understanding of their role as being to build sales “muscle” in their team, not just help push deals.


  • Inability to segment their team – Managers need to learn to adapt their leadership style to the different competencies of each sales rep on their team – teach the new hires, coach the mid-performers, and motivate the high achievers


  • Inefficient use of field travel time – too many managers focus field travel on helping “co-sell” instead of using this precious time to assess strengths and weaknesses


  • Poor quality of coaching conversations – most managers have a strong bias towards providing feedback and advice instead of having the quality questioning-based coaching conversations that deliver the “a-ha” moments to reps that drive lasting behavioral change.


Essential Features of Great Sales Coaching Software


CRM Integration

CRM integration is our #1 priority for implementing an effective sales coaching process.

Many so-called sales coaching platforms are not really platforms at all – they are stand-alone “apps” that take your team’s coaching workflow out of what is your true sales platform – your CRM! These external coaching apps tend to focused on general Human Resources metrics and only loosely connected to building selling capability. We prefer a tight focus on building sales “muscle”.

Coaching software that runs natively on you CRM (like HubSpot, Microsoft Dynamics, Salesforce.com) allows sales coaching to be tightly connected to the day-to-day deal workflow between managers and their sales teams. The best sales coaching software becomes part of your daily sales process.

Real-time messaging through your CRM, (for example, a rep asking for feedback on a pre-call plan prior to an important customer interaction), means that your sales reps can benefit from higher frequency in-workflow “micro-coaching”.

It also supports a more “data-driven” approach to coaching. Your account plans, field travel notes and sales call plans can feed your coaching engine, meaning sales manager coaching can be more objective and evidence-based – critical to gaining sales rep buy-in.

Finally, CRM integration also allows leaders can drill down to see planning, coaching and competency assessment records, driving greater accountability for their coaching.

People respect what you inspect.

Sales Competency Frameworks

Your sales coaching tools need to help change your sales managers’ mindset away from just coaching deals, to coaching their people.

The single biggest mistake we see in companies implementing sales coaching platforms is that they choose tools focused almost exclusively on coaching deals and pipeline. Most front-line managers are already great salespeople – coaching deals is not the weakness that most front-line managers suffer from – it is coaching people, behaviors and skills.

Pipeline analytics and revenue intelligence metrics are, of course, useful in their own right for rep performance assessments and forecasting, but a good coaching tool will be focused on the competencies and gaps for each sales rep. This requires a simple, configurable competency framework, allowing managers to start assessing the capability gaps that hold the mid-performing sales reps from the productivity of the top performers.

A good sales rep competency framework is simple, product-agnostic and focuses on these key competencies:

  • Territory Management – the ability to prioritize your time towards the largest opportunities in your territory.
  • Account Management – the ability to gain access to and influence the more senior decision-makers in the customer accounts early in the sales process.
  • Market Knowledge and Business Acumen – focus less on product knowledge (which can be built with simple onboarding and quizzes) and focus more on an understanding of the operational, financial and personal value propositions that the different stakeholders in your customer accounts really care about.
  • Selling Skills – Simply put, customer-facing skills – pre-call planning for important meetings, and execution skills – the ability to gain the intended “advance” from these meetings.

Field Travel Support

Maximizing the value of manager field travel is critical to building team capability. Your coaching software should support this process.

Competency assessment (surfacing a sales rep’s strengths and weaknesses) is one of the most important outputs from a manager’s day in the field. (Here’s why!) 

A good manager day in the field is built on:

  • The rep completing, and the manager reviewing, pre-call plans in advance for all the meetings that the team will take,
  • The manager allowing the sales rep to lead the customer calls,
  • Post-call coaching (using the pre-call plan as the basis for a debrief), and
  • The manager updating competency observations for the rep to support future coaching.

Good sales coaching software streamlines this by creating a simple actionable workflow for both the manager and rep in the field. Lifting win rates and closing deals faster follows as a direct result of this process.

Sales Team Competency Dashboards

Sales leaders have access to an almost unlimited array of pipeline analytics dashboards.

The best sales coaching software augments these with a different kind of dashboard – People Analytics. These dashboards should give sales leaders answers to simple but critical performance management questions such as:

  • “What’s the quality of coaching from my front-line managers“, and
  • “Which ones know how to really build sales capability in their teams”.

Coaching Cadence Management

Sales managers are regularly dragged away by CROs and VPs of Sales from coaching towards “fire-fighting”. In even the best sales teams, there tends to be a constant tension between the urgent and the important.

Good coaching software will keep managers “on task” with simple coaching plans per sales rep, the ability to set different check-in frequencies for different team members (based on individual needs), and automation reminders for both manager and rep to “close the loop” on coaching sessions.

Coaching cadences will tend to be set based primarily on the level of sales readiness and competence:

  • New hires and those still onboarding tend to need more training than coaching (“show and tell”), and a high frequency of manager engagement,
  • Mid-performing reps will quickly get tired of being “told how to sell” – this is where managers need to focus on true coaching, typically setting quarterly capability goals and checking in every 3-4 weeks, and
  • The top performers in a sales team don’t need much coaching at all – their managers should focus on setting good stretch goals, and on motivating the rep.

Other Considerations for Deploying Sales Coaching Software

The successful deployment of any new software to your team hinges as much on the messaging and your launch initiatives as it does on the quality of the software itself. Consider these issues as part of your deployment plans.


Quality Sales Manager Skills Coaching Program

In our experience, too much is invested in sales training for front line salespeople, and not enough in the front-line sales management.

  • Reviewing account plans and pre-call plans,
  • Competency frameworks and assessing rep competencies (“What good looks like”),
  • Segmenting your team, building individual coaching plans, cadences and leadership styles,
  • Maximizing field travel value, and
  • Role-plays to build observation skills (a critical skill since your managers don’t have the luxury of recording sales conversations and reviewing transcriptions)
  • Role-plays to understand the difference between coaching and feedback (more difficult than you might think!), and to practice productive coaching conversations.As you can see, this training program

This covers a lot of ground, and is best delivered in modules (not a one-off event), with checkins using the actual coaching software and live team data.

Make training materials available offline. And look for software solutions that incorporate training software into the coaching software itself for just-in-time reinforcement as reps and managers work their regular workflow.

Review your Manager Performance Metrics

Front line sales managers need to know that their sales leaders take coaching seriously. Yet we see many sales organizations set almost all their manager KPIs on (often short-medium term) revenue metrics.

Sales and sales operations leaders need to carefully consider how they trade off this quarter’s results vs future quarters’ productivity. Coaching is a slower burn investment but when implemented well, can deliver truly phenomenal and sustainable sales performance growth.

Your sales manager leaderboards and scorecards should reward the managers who can credibly describe their team’s competencies, strengths and weaknesses, and who can demonstrate that they can bring mid-pack sales reps closer to the productivity of the top performers. We all talk about “rain-makers” as individual contributors, but it is these managers who can truly be the most valuable members of your sales team.

If you need help designing suitable manager KPIs, contact us for advice.

Deploy Pre-call Planning as Part of your Sales Process

Pre-call planning for complex B2B sales teams is a frequently overlooked part of the sales process.

By their nature, “playbooks” that work in simple sales motions break down for complex sales that require bespoke call planning. A good, robust pre-call planning template can create an instant boost to a salesperson’s productivity in its own right. But as we have described above, pre-call plans also form a highly useful input to your field coaching engine – deploying both together can complete the circle.



When implementing field sales coaching software for your field sales managers, look for software that delivers the following:

  • Full integration with your CRM, so coaching is integral to the deal workflow
  • A configurable sales competency framework (“coach the people, not just the deals”)
  • Support for manager field travel
  • Drill-down competency dashboards to drive coaching accountability
  • Support for managing coaching cadences

And consider your deployment plans to gain buy-in:

  • Support your managers with quality manager coaching skills training,
  • Review your manager performance metrics to recognize and reward coaching performance, and
  • Implement pre-call planning as part of your coaching process deployment.


The Swagger Sales training curriculum is supported by SWIFTTM for Salesforce integrated planning and coaching tools – built right into your CRM.

  • Integrated call, account and negotiation planning tools
  • “Closed Loop Coaching” action plans drive sustainable capability development
  • Drill-down leadership visibility to planning, coaching and competencies
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Swagger Sales™ trains your team to perform better and gives you the tools to track progress.

The dashboards bring all the information into one place – it’s really about accountability, you can look at it very quickly to see if you have a problem in a certain area.

Kim Moller, Senior Vice President of Sales
MiMedx Group, Inc

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